I whipped up a script that essentially fixes the problem, but it's
working around what I suspect to be a driver or NetworkManager issue.

/etc/network/if.pre-up.d/hackwireless:
#!/bin/sh
iwconfig eth1 essid MYESSID
sleep 2

Replace your network interface name (eth1) and your wireless network's
ESSID (MYESSID), and chmod +x the file. From now on, NetworkManager
connects to my wireless network flawlessly every time. I tried simpler
things such as "iwconfig eth1 rate 11M" or "ifconfig eth1 up", but it
seems that setting your wireless ESSID manually before NetworkManager
kicks in is the only way to fix the issue. Setting a dummy ESSID also
doesn't help, it has to be your real ESSID.

What logs do you need to troubleshoot this issue?

-- 
NetworkManager cannot connect to WPA network at first boot
https://bugs.launchpad.net/bugs/103366
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